SPECIAL EVENTS
Gloucester Summer Kick-Off Carnival
Gloucester’s second annual Summer Kick-Off Carnival is the perfect place for thrills and memories
Arts at Abingdon by Gloucester Arts Festival
Part of the music series spanning over 37 years, Arts at Abingdon offers a collection of concerts featuring artists from many parts of the globe. All concerts are free of charge.
Gloucester Arts Festival Book Fair
The Book Fair is expected to draw book lovers, families, and community members of all ages, celebrating the vibrant literary scene in Gloucester and its surrounding areas.
Fathers Day Celebration - Zoll Vineyards
Join us at Zoll Vineyards for a Fathers Day Celebration!
Sports Star Screening by Gloucester Arts Festival
Let’s go to the movies! Join us for the 18 minute film with Gloucester native Ellis Finney, its writer/director, and Jeff Lichtenstein, the movie’s producer.
The Great Community Yard Sale at Brent and Becky’s Bulbs
Join us for a fun-filled day of bargain hunting at the gardens of Brent and Becky’s!
Seward Johnson Sculpture Walk by Gloucester Arts Festival
Sculpture enthusiasts rejoice as the exquisite masterpieces of renowned artist Seward Johnson make a dazzling comeback to the Gloucester Arts Festival.
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Concerts On The Green : Toby and Larry
Concerts on the Green Summer Series is back! Join us for free live music in the historic Court Circle on Main Street on select dates this summer.
Food Truck Frenzy
Fresh flavors, coastal vibes, family fun, music, and summer memories.
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
RiverJam 2026 by Arts On Main
Enjoy great music from the Ballast Band, Edison & Company, and RaJazz! Try delicious food from local vendors and plan for lots of fun and dancing!
Gloucester Wine Festival
One of Gloucester’s favorite fall traditions- the annual Wine Festival!
Skydog Concert at Flat Iron Crossroads
Skydog, based in Richmond, Virginia, has earned acclaim for its uncanny ability to transport audiences back to the late 1960s and early 1970s with their faithful recreation of the Allman Brothers Band’s iconic sound.
Plein Air Gala by Gloucester Arts Festival
Join us for the culmination of the week-long plein air competition for the spectacular Gala at the Fine Arts Museum of Gloucester!
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Concerts On The Green : Mike Reed Music
Concerts on the Green Summer Series is back! Join us for free live music in the historic Court Circle on Main Street on select dates this summer.
Symphony Under The Stars by Gloucester Arts Festival
Celebrating two decades of making music accessible to everyone! Join us for the spectacular Symphony Under the Stars FREE Family Concert and be part of this unforgettable anniversary celebration!
Paint Main by Gloucester Arts Festival
Celebrating 10 years of the Gloucester Arts Festival.
Brews, Brine & Wine by Gloucester Arts Festival
Celebrating 10 years of the Gloucester Art’s Festival!
Marine Science Day by VIMS
One day the year only, join VIMS for exhibits, tours, activities, and food!
SOLD OUT Abingdon Ruritan Club Seafood Festival
Gloucester’s biggest all-inclusive seafood festival! Join this bi-annual sell out event!
Purely Natural Pop-Up at Brent and Becky's Bulbs
Favorite local vendors and bath salt workshop at famous Brent and Becky’s Bulbs
Annual Luau at Gloucester Brewing Company
Celebrate the start of summer with Gloucester Brewing Company’s biggest event of the year.
Concerts On The Green : Clan McCool Band
Concerts on the Green Summer Series is back! Join us for free live music in the historic Court Circle on Main Street on select dates this summer.
Gloucester Farmers Market at Historic Ware Church
Gloucester’s best pop-up market, every 2nd Saturday May through September.
Florencia & the Feeling at Flat Iron Crossroads
Blending upbeat funky rhythms, heartfelt songwriting, soaring four-part harmonies, and a touch of jazz and Latin flair
Pressing Strings at Flat Iron Crossroads
Blend of blues, rock, and folk, wrapped in soul-stirring storytelling and toe tapping grooves.
Persophone's Return: Dinner and Gala at Zoll Vineyards
Theatrical dinner with award winning wines.
2026 Historic Garden Week
The 2026 Historic Garden Week Tours are blooming across Virginia — and the Gloucester/Mathews Tour will take place on Saturday, April 18th!
Machicomoco's Earth Day Celebration
Education, activities, and food vendors at picturesque Machicomoco State Park.
Symphony Under the Starts by Gloucester Arts Festival
Celebrating two decades of free music and 10 years of the Gloucester Arts Festival.
Secondhand Saturdays
Celebrating Gloucester’s most charming thrift, antique, and boutique retail through a lens of sustainability.
Gloucester Daffodil Show
Don’t forget to visit the Gloucester Daffodil Show during your visit to the 40th Gloucester Daffodil Festival!
Gloucester Daffodil Festival
Join Gloucester’s most cherished celebration to kick-off spring! The 40th Gloucester Daffodil Festival lights up Main Street on March 28 & 29, 2026.
Green Leaf Society at Flat Iron Crossroads
Join Flat Iron Crossroads for their St. Patrick’s Day Celebration with Green Leaf Society.
Carter Minor Blues Band at Flat Iron Crossroads
Join Flat Iron Crossroads for the Carter Minor Blues Band!
Timberneck Tea
Join the Fairfield Foundation for their 4th annual Timberneck Tea at beautiful Machicomoco State Park.
Working Waterfronts Photography Exhibition Opening Reception
Each photograph reflects not just a moment in time, but a deeper narrative about livelihood, legacy and the quiet strength required to survive — and thrive — where land meets water.
Tin Can Fish Band at Flat Iron Crossroads
Enjoy folk, rock, and roots music by Tin Can Fish Band at Flat Iron Crossroads.
XTRA Home and Garden Showcase
Join WXGM for their 14th annual Home and Garden Show at the Gloucester Moose Lodge.
Dive into what the locals love.
View all the local programs and events cherished by the Gloucester community, welcoming friends from near and far with open arms.